Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from AED 256

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26 Nov - 27 Nov
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27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
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5 Dec - 7 Dec

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Compare 845 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1005)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 390
AED 436 total
includes taxes & fees
17 Dec - 18 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
The price is AED 229
AED 256 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (803)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is AED 340
AED 380 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Untold
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very Good, (787)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is AED 262
AED 299 total
includes taxes & fees
30 Nov - 1 Dec
Candlewood Suites West Springfield by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 473
AED 672 total
includes taxes & fees
30 Nov - 1 Dec
The Cornell Inn, Lenox & The Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (971)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 328
AED 366 total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is AED 530
AED 756 total
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (790)
"Place was great!"
United States
Benjamin
The price is AED 391
AED 488 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 350
AED 391 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (698)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is AED 393
AED 439 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1004)
"Great like always "
United States
Sharee
The price is AED 304
AED 348 total
includes taxes & fees
3 Dec - 4 Dec
Red Roof Inn PLUS+ West Springfield
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (766)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (98)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AED 400
AED 447 total
includes taxes & fees
3 Dec - 4 Dec
River Valley Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Indoor pool
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
Metro Center
8.2 out of 10, Very Good, (1306)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is AED 406
AED 460 total
includes taxes & fees
30 Nov - 1 Dec
La Quinta Inn & Suites by Wyndham Springfield MA
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is AED 490
AED 547 total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Check-in/check-out kiosk
Quality Inn West Springfield

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1019)
"Room and staff were good "
United States
George
The price is AED 309
AED 354 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn West Springfield
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2262)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is AED 314
AED 365 total
includes taxes & fees
3 Dec - 4 Dec
D. Hotel Suites & Spa
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (756)
"Clean room, very courteous staff "
United States
Thomas
The price is AED 555
AED 619 total
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
View from property
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (570)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is AED 434
AED 497 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott West Springfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping, and forests in Chester!

See all hotels in Chester
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"beautifully renovated, excellent staff, quiet, great breakfast"
Mark 2-night trip
Posted 14 hours ago
The Ellery

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is AED 309 per night from Dec 14 to Dec 15
AED 309
AED 354 total
14 Dec - 15 Dec
includes taxes & fees
7/10 Good! (1,017 reviews)

Hotels in Chester with star-rating

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 km) from the heart of Chester, is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Berkshire Mountain Lodge and D. Hotel Suites & Spa. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation rentals in Chester?
Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Chester is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
For additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.
What's the best accommodation near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer including the waterfalls, shopping, and riverfront. Tourists can also enjoy the city's restaurants, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
A favorite place to visit is Chester Town Hall. You'll also find Pyramid Lake and Skyline Trail in the area. Check out what more to see and do in Expedia's Chester guide.
What's the seasonal weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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